Brian Sher's determined journey from the William Morris mailroom to 'Boss'

Executive producer Brian Sher on the Chicago set of the Starz drama 'Boss' with star Kelsey Grammer.

Executive producer Brian Sher on the Chicago set of the Starz drama 'Boss' with star Kelsey Grammer.

David ZurawikThe Baltimore Sun

A decade after graduating from Baltimore’s Gilman School, some alumni might be vaulting up the ladder in careers as executives or politicians. But Brian Sher, Class of ‘86, was looking at the lowest rung — starting out as a trainee in the mailroom of a Hollywood talent agency.

After attending Tulane and the University of Southern California, Sher had tried doing most of the things young people do to break into show business: working as production assistant on a movie, playing a walk-on character and writing a screenplay.

Then one night, a friend who was an agent took him to dinner, looked him in the eye and asked him what the expletive deleted he was doing with his life. He suggested Sher go back and learn some real show business skills the old-fashioned way: by starting in the mailroom of the famed William Morris Agency.

Since then, Sher has climbed through every level of the agency business from finding and selling feature film scripts like “Serendipity” and “Hitch,” to packaging such productions as “The Great Debaters” with Denzel Washington.

Today, he has his own Hollywood management-production company, Category 5 Entertainment, which includes working relationships — and friendships — with such lightning-rod figures as the rapper-actor T.I.and Philadelphia Eagles quarterback Michael Vick.

He is also partners with Kelsey Grammer in the actor’s production company, Grammnet NH, and one of the executive producers of the Starz drama, “Boss,” which begins its second season Friday night. Grammer won a Golden Globe last year for his portrayal of Tom Kane, the terminally ill mayor of Chicago raging against the dying of the light and fighting to hold onto power. The series was nominated as best drama.The one-time “Frasier” star calls his partner “extraordinary.”

“Brian has the vitality and the kind of energy I needed to remake my company,” Grammer said last week about his partnership with Sher. “The other thing he has is an eye for great material, and that is the most important piece of the puzzle in the end. All of that puts him a category that I find extraordinary. And so, I made a big pitch to get him to join me in the company and put some shows together.”

At 44, the still boyishly handsome Sher — the son of Baltimore TV personality Richard Sher — has incredible energy. A sitdown interview quickly becomes a stand-up, walk-around, leave-the-room-and-return experience in which Sher not only answers questions with a burning intensity, but suggests further ones, along with photo possibilities. He’s accommodating yet relentless — a hallmark of his business style.

“Boss” is the first show that Sher helped Grammer put together. After meeting Grammer through producing partner Stella Bulochnikov, Sher put the Emmy-Award-winning actor together with one of his writer clients, Farhad Safinia, who had written and produced “Apocalypto” with Mel Gibson.

“We all met for lunch at the Four Seasons in Beverly Hills, and Farhad and Kelsey hit it off,” Sher says. “They started waxing poetic about ‘King Lear,’ which is what ‘Boss’ is, and Cordelia, and all those characters. And by the end of our Bloody Mary lunch, they had come up with the idea of the modern-day ‘King Lear’ set in the world of politics.”

Once Safinia wrote the script, Sher took it to the uber-agent he shares with Grammer, Ari Emanuel, who said, “We have to find a great director.”

“We needed that last piece,” Sher says. “We had the script and we had the star.”

Emanuel represented Gus Van Sant, who had just been nominated for an Oscar for the feature film, “Milk.” But Van Sant said that while he was flattered, he didn’t do television.

Sher recalls, “And Ari said — as only Ari can do it — ‘I hear you. I don’t care what you say. Read the script and call me tomorrow and tell me you’re in.’”

Van Sant liked the script so much that he agreed to direct the pilot and stay on as executive producer.

This is what’s known as “packaging” in Hollywood — and this is the skill that Sher came to believe he might have while working his way up from the mailroom at the William Morris Agency. He’s been honing that ability the last 15 years at places like ICM (International Creative Management) and now his own Category 5.

He moves in the world of the Ari Emanuels. In fact, you can see Sher in a few episodes of “Entourage” playing an agent who gets yelled at by Ari Gold, the Ari Emanuel-like agent played by Jeremy Piven. Sher’s not an actor; his cameos are an inside-inside joke among Hollywood talent agents.

There’s a small inside joke for Baltimore viewers in episode five of “Boss” this season. The moderator of a televised political debate is played by Richard Sher.

“When he was 8 years old, Brian co-starred with the late Tony Randall in ‘The Music Man’ at the Mechanic Theater,” the former WJZ newsman says. “OK, he was actually only in the kids' chorus. But Annabelle [Brian’s mother] and I knew then that Brian was headed for a career in show business. Now he can rap with T.I., act with Kelsey Grammer or toss a football with Michael Vick. We're very proud.”

In addition to his work with Grammer, Sher produced “The Michael Vick Project,” a reality series with the Philadelphia Eagles quarterback for BET, and the “Road to Redemption” reality series with rapper T.I. for MTV.

On Sept. 3, another collaboration between Sher and T.I., the reality series “T.I. and Tiny: The Family Hustle” will start its second season on VH1. Sher works with T.I. and Vick in several show-biz realms. He helped the former land a role on “Boss” this season, and in July, he partnered with Vick in launching a clothing line, Michael Vick’s V7.

While Vick and T.I., whose real name is Clifford Harris Jr., are thriving professionally at the moment, neither was exactly a can’t-miss client or partner at first.

“Road to Redemption” features T.I., who was about to go to prison on a federal weapons charge himself, interceding in the life of a troubled teenager each week. It was the first TV show Sher produced.Vick saw “Road” while he was in prison for running a dog-fighting operation. And upon his release in 2009, he called Sher.

“I got a phone call out of the blue from Michael Vick who had been out of prison three days,” Sher says. “Didn’t know him, had never met him. He said, ‘I saw your show while I was in prison, and I want to tell my story in the same tone, in the same way. I called T.I., and he said you’re the man I have to talk to.’”

Sher says he was skeptical but instantly flew East to meet with Vick.

“I flew to Washington Dulles on Memorial Day weekend three years ago,” Sher remembers. “I rented a car, drove 300 miles to Hampton, Virginia. All the news media crews were out there, and I knocked on the door, and Michael Vick answers in shorts, T-shirt and an ankle bracelet.”

Sher says they sat on a back porch and talked into the night while mosquitoes ate them alive.

“He basically said to me, ‘I completely ruined my life. I had more than $100 million, I had endorsements, I was an all-pro quarterback of the [Atlanta] Falcons— and I lost it all. I’ve got nothing. I owe more money to more people than I even know — creditors, bankruptcy. So, I’d like to tell my story.’”

“I saw his two very young daughters crawling around, and he was a dad like me,” says Sher, the father of a 10-year-old boy, Jake, and 8-year-old girl, Samantha. “Obviously, what he did was horrible and wrong, and he knew that and acknowledged that. But he wanted people to know where he came from and how and why this unfolded in his life.”

Calling Sher a “great friend,” Vick says the relationship was cemented that first night as well.

“You know, I just thought coming out of prison, a lot of people would be hesitant,” Vick said in a telephone interview last week. “But he was one of the first people that showed a great deal of commitment and helped me turn my life around.”

To Vick, it seemed as though Sher arrived in Virginia from California only hours after they first spoke. He was impressed with Sher’s “great drive and ambition.”

“That’s what you have to like about him: his dedication and commitment,” Vick said. “His dedication to our friendship means a lot to me.”

T.I. says his film and TV career might not have happened without Sher in his corner.

“He's been going hard for me from Day One,” the actor-rapper said last week of their six-year relationship. “People wonder how I got into ‘American Gangster,’ or how I got in ‘Boss’ with Kelsey Grammer and all the other phenomenal opportunities in film and television I've gotten. The answer is that Brian’s been a huge part of all of it. He's been an incredible instrument.”

Judging by the first three episodes of season two of “Boss” made available for preview, T.I. has repaid Sher’s confidence in his TV talents. He brings energy and a strong screen presence to the role of a Chicago drug dealer looking to find political power in Kane’s city hall.

Sher doesn’t work with anyone he doesn’t “believe in,” T.I. says. “But once he's in with you, he goes to the ends of the Earth, man. And there's nothing he won't do to get you to where he believes you have the potential to be. He just goes all out.”

That’s another thing Sher says he learned in his journey from the William Morris mailroom to owning his own agency: the kind of 24/7, there-are-no-days-or-nights-off commitment it takes to succeed in Hollywood.

“I think what I found when I went back and started in the mailroom is a world I could excel in if I worked very, very hard,” he says, recalling a 2 a.m. phone call he received last week from T.I. who had an issue that required immediate attention.

“It’s not a world you can go to college or graduate school for. There’s no blueprint for what I do. You have to trust your gut and, in the end, you absolutely have to outwork the competition.”

He’s learned other, very Hollywood lessons along the way, too.

While he says he treasures his friendships with partners and clients like T. I. and Vick, “The key is to never lose sight of the fact that they are first and foremost counting on me to serve a certain function in their business lives, and I am careful to never get that twisted. When I was his agent, Denzel Washington used to always say to me, ‘This ain't show friends. It’s show business.’”

‘Boss’Season 2 premieres 9 p.m. Friday on Starz

Brian Sher at a glance:

Education: The Gilman School, Tulane University, University of Southern California

Baltimore credits: Worked as a production assistant on “Homicide: Life on the Street” and had a walk-on appearance on “Avalon”